Basic information Safety Supplier Related

(R)-(+)-WARFARIN

Basic information Safety Supplier Related

(R)-(+)-WARFARIN Basic information

Product Name:
(R)-(+)-WARFARIN
Synonyms:
  • 4-Hydroxy-3-[(1R)-3-oxo-1-phenylbutyl]-2H-1-benzopyran-2-one
  • (R)-4-hydroxy-3-(3-oxo-1-phenylbutyl)-2-benzopyrone
  • (S)-3-(alpha-Acetonylbenzyl)-4-hydroxycoumarin
  • r-(+)-3-acetonybenzyl)-4-hydroxycoumarin
  • 2H-1-Benzopyran-2-one, 4-hydroxy-3-(3-oxo-1-phenylbutyl)-, (R)-
  • 2H-1-Benzopyran-2-one, 4-hydroxy-3-[(1R)-3-oxo-1-phenylbutyl]- (9CI)
  • Coumarin, 3-(a-acetonylbenzyl)-4-hydroxy-, R-(+)- (8CI)
  • Dextrowarfarin
CAS:
5543-58-8
MF:
C19H16O4
MW:
308.33
EINECS:
226-908-9
Product Categories:
  • Aromatics
  • Chiral Reagents
  • Heterocycles
  • Intermediates & Fine Chemicals
  • Pharmaceuticals
Mol File:
5543-58-8.mol
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(R)-(+)-WARFARIN Chemical Properties

Melting point:
≥170 °C
Boiling point:
515.2±50.0 °C(Predicted)
Density 
1.307±0.06 g/cm3(Predicted)
storage temp. 
2-8°C
solubility 
DMF: soluble
pka
4.50±1.00(Predicted)
form 
A crystalline solid
color 
white to pale yellow
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Safety Information

Hazard Codes 
T
Risk Statements 
61-48/25-52/53
Safety Statements 
53-45-61
RIDADR 
UN 2811 6.1/PG 1
WGK Germany 
3

MSDS

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(R)-(+)-WARFARIN Usage And Synthesis

Chemical Properties

White Solid

Uses

(R)-(+)-warfarin has been used to investigate whether enantiomers of warfarin stereoselectively interact with pregnane X nuclear receptor (PXR) to upregulate main drug/xenobiotic-metabolizing enzymes cytochrome P450 3A4 (CYP3A4) and cytochrome P450 2C9 (CYP2C9). It has also been used in HepG2 cells to study protein profiles

Uses

The R-(+)-form of Warfarin (W498500). Coumarin anticoagulant.

Definition

ChEBI: (R)-warfarin is a 4-hydroxy-3-(3-oxo-1-phenylbutyl)-2H-1-benzopyran-2-one that has (R)-configuration (the racemate is warfarin, an anticoagulant drug and rodenticide). It is a conjugate acid of a (R)-warfarin(1-). It is an enantiomer of a (S)-warfarin.

General Description

The chiral carbon at position 9 produces two enantiomers, R- and S-warfarin. Commercially available warfarin (Coumadin or Jantoven) is a racemic mixture of S- and R-enantiomers.

Biochem/physiol Actions

Warfarin acts as a vitamin K antagonist. It is widely used to treat thromboembolic disorders. (R)-warfarin interacts with pregnane X receptor (PXR) and induces cytochrome P450 3A4 (CYP3A4) and CYP2C9 mRNAs expression in primary human hepatocyte cultures.

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